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Structure Database (LMSD)

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Common Name

11beta-13,14-dihydro-15-keto PGF2alpha

Systematic Name

9S,11R-dihydroxy-15-oxo-5Z-prostenoic acid

Synonyms

11beta-dhk-PGF2alpha
11beta-13,14-dihydro-15-keto Prostaglandin F2alpha
11beta-dhk-PGF2a

LM ID

LMFA03010203

Formula

C₂₀H₃₄O₅

Exact Mass

Calculate m/z

354.240626

Sum Composition

FA 20:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

11β-13,14-dihydro-15-keto PGF2α is a metabolite of PGD2 in the 15-hydroxy PGDH pathway.^1,2 Infusion or inhalation of tritiated PGD2 in normal males results in the appearance of peak levels of both 11β-PGF2α, as the immediate product, and 11β-13,14-dihydro-15-keto PGF2α in the plasma within 10 minutes.¹ Homogenates of human lung metabolize PGD2 first to 11β-PGF2α and then to 11β-15-keto-PGF2α in the presence of NAD+, but not 11β-13,14-dihydro-15-keto PGF2α.² Guinea pig liver and kidney homogenates metabolize PGD2 to 11β-13,14-dihydro-15-keto PGF2α, via 11β-PGF2α, in the presence of NAD+ and NADP+.²

This information has been provided by Cayman Chemical

References

1. Robinson, C., Hardy, C.C., and Holgate, S.T. The metabolism of prostaglandin D2 after inhalation or intravenous infusion in normal men. Biochim. Biophys. Acta 963(2), 151-161 (1988).

2. Robinson, C., Herbert, C.A., Bedwell, S., et al. The metabolism of prostaglandin D2. Evidence for the sequential conversion by NADPH and NAD+ dependent pathways. Biochem. Pharmacol. 38(19), 3267-3271 (1989).

String Representations

InChiKey (Click to copy)

VKTIONYPMSCHQI-KGILNJEGSA-N

InChi (Click to copy)

InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,18+,19+/m1/s1

SMILES (Click to copy)

[C@H]1(CCC(=O)CCCCC)[C@@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O